TWI342330B - Liquid crystal composition for use in bistable liquid crystal devices - Google Patents

Abstract

The invention is directed to the use of a liquid crystal composition in a bistable liquid crystal device and especially in a zenithal bistable nematic liquid crystal device, a nematic liquid crystal medium, and a bistable liquid crystal device comprising the liquid crystal composition whereby said liquid crystal composition comprises at least 30 weight % (based on the total weight of the composition) of a component (alpha) containing one or more compounds having a dielectric anisotropy Deltaepsilon of at least 25, whereby at least 25 weight % (based on the total weight of the composition) of said compounds have a dielectric anisotropy Deltaepsilon of at least 40; and at least 5 weight % of a component (beta).

Description

1342330 玖Invention Description: [Technical Field] The present invention relates to a liquid crystal composition for use in a dual stable liquid crystal device, and more particularly to a dual point stable nematic liquid crystal device, and a nematic liquid crystal medium And a dual stable liquid crystal device comprising the liquid crystal composition. [Prior Art] Optoelectronic devices that display information using liquid crystal media are well known and used in a wide variety of technical applications (for review, see H. Kawamoto, Proc. IEEE, 90, 460 (2002)). Among them, the nematic liquid crystal display device is the most excellent; for example, a twisted nematic (TN) liquid crystal device (M. Schadt & w. Helfrich, APPl. Phys Lett., 18, 127 (1971)) and a super-twist type. Nematic (STN) liquid crystal devices (see especially TJ Scheffer and J. Nehring, Appl. Phys. Lett., 48, 102 1 (1984)). The devices are in a single steady state, i.e., the liquid crystal medium is switched to the "on" state by applying an appropriate voltage, and is switched to the "off" state when the applied voltage is lower than the lower voltage value. In order to display complex information, the optoelectronic device must include several image elements that can be switched independently of each other. However, when using direct or even more f-calling images (4), the number of addressable elements in the ship's liquid crystal display is limited. In the first case, there is only the geometrical requirement of the electrical connection and in the second example, the device conducts the voltage. Excessive requirements for the curve. This limitation can be overcome by incorporating a thin film transistor (TFT) into each of the portrait elements. This device, also known as an active matrix (AM) display, allows a high number of portrait elements to be addressed and thus has a large area of high resolution display with relatively low voltage requirements. Some of these devices are also preferably mechanically stable and have a wide temperature range of 88881 .doc 1342330. While this can be a small portable battery powered display, this technology has some drawbacks for some applications. The manufacture of alpha-μ displays is still a complex process, including the creation of complex assemblies, which are responsible for high manufacturing costs. Since the device does not have intrinsic or intrinsic memory, the display requires periodic updates even for still images. This causes a considerable power consumption and thus a loss of battery life. This is especially undesirable for portable tape-mounted displays or wired-part displays that are only charged over time, such as mobile phones, personal digital assistants (PDAs), pagers, electronic display end labels, and the like. One way to avoid the limitations and disadvantages of such nematic liquid crystal display devices is to use displays having internal memory effects, such as dual stable liquid crystal devices. The bistable state means that the liquid crystal medium molecules inside the device can adopt two (or evening) different stable states. As a result, the liquid crystal molecules of the medium are switched to the first stable state by applying a suitable addressing scheme, which is sustainable even after addressing; the liquid crystal molecules are subjected to the second stable state by using an alternative scheme, which is also after addressing. Still sustainable. A ferroelectric liquid crystal display using a smectic liquid crystal material can be made into a dual stable, 'device, however' it has several disadvantages such as lack of impact resistance, narrow operating temperature range, and low cell gap i, resulting in manufacturing difficulties. . therefore,

The double stability of the switching of the cracks is shown in J. Iz Dozov et al. "Development of the anchored broken display (BiNem®)", 8888l.doc 1342330

Proceedings SID 01 (2001), 16.1, 224 and its references) a promising approach to achieving dual stability in nematic liquid crystal displays is to use surface alignment of two or more stable states of the building. As discussed in the literature (see, for example, JC Jones, G. Bryan-Brown, E' Wood, A. Graham, P. Brett, and J. Hughes, "Liquid Crystal Materials, Devices, and Flat Panel Displays" " The main dual stable state liquid crystal display ", R. Shashidhar, B.

Edited by Gnade, SPIE Proceedings, Vol. 3955 (2000), 84 and references cited therein, can distinguish between azimuthal and zenithai dual stable states. In the first example (ie, equidistant azimuth dual stabilization), the director of the liquid crystal molecules in the raster-aligned display on the surface of one of the panel plates (or substrates) of the display will be parallel to the two stable states. This is set in the plate; this means that the switching between the steady states occurs in the plane of the display panel (see, for example, WO 92/00546 and WO 95/22077, which describes the use of a substrate having a double grating alignment layer)^ However, the rework selectivity of this steady state is found to be difficult and switching generally requires high switching voltages. On the other hand, a double double stability is observed when using a pole double stable state surface (see Figure 1; the thin line represents a local guide of liquid crystal molecules oriented by interaction with a surface grating and a suitable alignment layer) . By this surface, the liquid crystal molecule director has two possible configurations which have different pretilt angles in the same isometric azimuthal plane (i.e., the plane perpendicular to the substrate surface of the display liquid crystal cell). The first state is a high tilt state and the second state is a low tilt state. The grating of the pole double stable surface is defined by the amplitude a and its spacing L; the value of L is generally about 米6 to "88881.doc 1342330".

Micron (see WO 97/14990 and details see %〇〇2/〇8825; and JC Jones, G. Bryan-Brown, E. Wood, A. Graham, P. Brett^J. Hughes Liquid Crystal Materials, Devices and Plates Display, in the "new double stable liquid crystal display based on grating alignment", R. Shashidhar, B

Gnade, ed., SPIE, Vol. 3955 (2000), 84). The vertical alignment orientation can be induced, for example, by coating the grating with a vertical alignment layer; this orientation ensures that the director of the liquid crystal molecules is not disposed in parallel with the grating trench. Although the director of the liquid crystal molecules is oriented perpendicular to the (partial) surface, that is, as the surface changes along the direction perpendicular to the groove, the "bulk" The effect of relative surface alignment in the state. Switching from one steady state to another can be achieved by applying a simple electrical pulse, thereby causing the black display or portrait element to switch to white (or vice versa) with proper polarizer configuration and blocking and when applying opposite polarity pulses Black occurs to switch to the original state and white to black (or vice versa). Switching can also be induced using a voltage of the same polarity but a much higher voltage (also known as "reverse switching"); however, the inverse switching adverse effect limits the operation of the pole double stable nematic device in addressing and therefore Limiting the high voltage that may be required for reverse switching. Generally, for obtaining the pole double stable state, only one of the substrates of the two display liquid crystal cells is provided with a surface grating. The opposite plate may have a vertical alignment of liquid crystal guides. The surface (VAN mode, see Fig. 2a) or the surface on which the guide plane is arranged (twist mode, see Fig. 2b) thus causes the liquid crystal director to twist around the axis of the liquid crystal cell which is perpendicular to the substrate through the low tilt state. Learning and configuration, indeed LCD module parameters 'addressing means, 88881.doc -9- 1342330 The entire pole dual stable state device assembly (including the use of polarizers) and other details, see WO 97/14990, EL Wood, GP Bryan-Brown, P. Brett, A·Graham, JC Jones and JR Hughes "Pole Dual Stability Devices for Portable Applications (ZBDTM)&quot ;, SID 00 Digest (2000), 124, JC Jones, JR Hughes, A. Graham, P. Brett, GP Bryan-Brown and EL Wood " pole double steady state device: for e-books with simple LCD ", iDw'oopooo), 3 () 1, jc · jones, s. M_ Beldon and EL Wood, "Grayscale of Extremely Dual-Stability LCD: Path to Ultra-Low Power Color Display", in September 2002 Seminar on the 2002 ASID meeting of the Singapore Information Display Association; and a detailed discussion can be found in J c

Jones, G. Bryan-Brown, E. Wood, A. Graham, P. Brett and J.

Hughes, "Liquid Crystal Materials, Devices, and Flat Panel Displays" in the "Glass Alignment-based Newly Stable Dual-Energy Liquid Crystal Display", R. ShasMdhar, B Gnade, ed., SPIE, Vol. 3955 ( 2〇〇〇), 84 and the literature cited therein. The use of pole double stability in optoelectronic devices achieves attractive features: image orientation on the display without the need to continuously update high mechanical shock stability with low power consumption because the display only needs to be addressed when the image changes Infinite multiple degrees of freedom for unrestricted analysis without the need for tft components to transmit and reflect the suitability of the plastic substrate. In addition to the configuration and configuration of the pole dual stable state display, the pole double stable state device technology is another - mainly The problem is a nematic liquid crystal medium used inside the display cell. 8888l.doc -10- 1342330 The pole double steady state device and therefore the liquid crystal medium must meet several requirements that are more or less relevant to the particular use of the device. Since there is no consistent theory of predictable optimal physical variables to date, it may be useful to use a set of (semi-) experimental parameters for evaluating the usefulness of liquid crystal media in their pole-double stable nematic devices. These are the so-called r-V curves used to switch the pulse duration 7> and the voltages used to switch the 丨〇 and 9〇% values in opposite polarities (see Figure 3), i.e. Merck KGaA, in prior art liquid crystal mixtures.

MLC-6204-000 of Darmstadt, Germany. First, in order to minimize power consumption, in order to make the portrait element of the device address more freely and to maintain within the limits of a standard STN driver, a low switching field is used to switch from one dual stable state to another. And the corresponding low operating voltage is required. In terms of material comparison, in a given test cell providing a double stability of the pole, a pulse switching electric field of a switching voltage V of a specific liquid crystal mixture, for example, a transmittance change from 90% to 90% can be determined. Generally 1 microsecond pulse duration). (Usually, you can also use white-to-black (W_B) i100 to 1〇% transmittance change to turn away' where the switching electric field can be higher or lower than the B-w transition, depending on the shape and size of the light. ). In order to consider the voltage drop across the grating (which varies with the type of grating and the thickness of the cell), the measured E value is corrected to distinguish the electric field that passes through the liquid crystal and is again used to obtain a 1 〇〇 microsecond pulse. Correct the comparison purpose of the switching electric field ELC@1(10)Ws. Here, when calculating the electric field just passing through the liquid crystal, an additional factor of 15 micrometers is added to the thickness of the liquid crystal cell: E_s = V_s / d and ELc ^ oof VHx ^ / CcI + l. S), where d is in micrometers.

Elc^oom multiplied by the optimal cell gap d (jpt (can be estimated using TN first minimum 8888l.doc • 11 - 丄342330 pieces of dopt Λ ν3/(2Δη)); ^ = 555 nm and liquid crystal dielectric J · The production voltage V°pt corresponding to the optimal cell gap of the liquid crystal only for microseconds. The heart_°" and V〇pt vary depending on the liquid crystal medium used. The best cell gap (see Figure 2b), but the VAN form can still be compared here (see the picture), the blocking effect of the 0-mixing state will match the half-wave plate of the rectangular wave plate, and the polarizer structure The type depends on dAn=X/2 and (!Δη=λ/4). The second experimental parameter considered is the window AVcpi corresponding to the optimal cell gap. Effect: When a pulse is applied with a predetermined time sIot of 4 〇〇 microseconds and a defined pulse polarity such as B w , the desired switching can be observed at a specific value of the switching electric field and not due to the pulse of the reverse polarity. Induction is a further inverse switching induced by a pulse of the same polarity when the switching electric field is increased (in this case, for example) For example, W_B) For technical purposes, 5, obviously the operating window is of course as wide as possible to make the driving diagram used more free and especially for achieving good grayscale operations (see jc Jones, SM Beldon and EL Wood, 'The gray level in the double-dense LCD: the path to the ultra-low-power color display', the presentation of the 2000 ASID meeting of the Information Display Association, which can be expressed, that is, for the 400 microsecond pulse, Correction difference between 90% inverse switching electric field and 9〇% B_w switching electric field: △E4〇〇ws=AV4〇〇“s/d and ΔΕιχ; @4〇〇/<5=Δν4〇0«5 (< 1+1.5) ' where d is micro-ancient. Consider the best cell gap dQpt multiplied by △£[(:@4()()"5 to get the best 囱V0pt (d0ptAELc@4〇 o»s=AV〇pt). The optical response time T〇pt corresponding to the optimum cell gap—parameter 88881.doc -12- 1342330 describes how the liquid crystal medium changes rapidly between steady states after applying an electrical pulse. It can be determined by measuring the response time τ of 1 BW conversion using a 1 〇〇 microsecond pulse in a positive test cell. Then, in order to make the experimental value nominal, multiply by (dopt/d)2 to obtain T〇pt (d()pA. The best cell gap and v for the test cell are used. The cell gap is). The W_B transition is faster (less than 1 millisecond) and therefore the BW response time is indeed of the utmost importance when evaluating the properties of the liquid crystal medium used. τ. ^ The smaller the optical medium, the faster the optical response. A small r〇pt (about 4 〇 milliseconds or less) is needed for some optoelectronic applications, such as displaying moving images. Even better for a particular video application than less than about .16 milliseconds and thus no flash is observed. Yet another important parameter is the clearing point τ 液晶 of the liquid crystal medium, which describes the temperature at which the nematic mixture becomes anisotropic. For many technical purposes and to the variability of optoelectronic devices (and possibly applications) that utilize extreme dual stability, liquid crystal media having a high degree of transparency (preferably at least 80 〇 C) are required. Such liquid crystal media used in pole double steady state devices have been described in the prior art as not meeting all of the above parameters. Even liquid crystal mixture mlc_6204_000 (available from Merck KGaA, Darmstadt, Germany) as a preferred medium in a pole double stable state device (w〇01/40853 'Example 6, J'C. Jones, G. Bryan-Brown, E Wood, A. Graham, P. Brett and

Hughes, "Liquid Crystal Materials' Devices and Flat Panel Displays „, a novel bistable liquid crystal display based on grating alignment,|, R Shashidhar, B Gnade, ed., SPIE, Vol. 3955 (2〇〇〇 ), 84) has only 62.4. The transparent point of N is slightly lower for 8888l.doc • 13-1342330 used for many possible pole-to-parallel dual-state devices. [Invention] It is a problem to provide a liquid crystal composition suitable for a dual stable liquid crystal device and particularly suitable for a pole double stable nematic device and having improved properties. This problem can be solved by using a liquid crystal group & The device is preferably a pole nematic liquid crystal device, and thus the composition comprises: at least 30% by weight (based on the total weight of the composition) of components (呦, which contain one or more of them having a dielectric a compound having an anisotropic Δ ε of at least 25, wherein at least 25% by weight (based on the total weight of the composition) of the compound has a dielectric anisotropy Δ ε of at least 40; and comprises at least 5% by weight (0); wherein the component (/ 3) comprises a compound and / or at least one compound of formula IV and / or compound and / or at least one compound of formula VI and / or at least one compound of formula VII at least one compound of formula m is at least one compound of Formula v:

III 88881.doc -14-

V

1342330 wherein a and b are independently 0 or 1; R", R32, R41, R42, R5i, r52 丨6丨, r62, r71 and r72 are each independently a Cl_Cl5 alkyl group which is unsubstituted or via CN or halogen. Mono or oxi-substituted and one or more of the CH 2 groups may be independent of each other, climbing-0-, -s-, -CH=CH-, -Cs c-, -CO-O-, -〇c_〇_ permutation 'Making heteroatoms not adjacent to each other; L31 is Η or F; _C0·0-, -CH2〇-, -〇ch2-, -cf2o-, -〇CF2-, -CH2CH2- s -CF2CF2- ' - CH2CF2-^-CF2CH2-^-CH=CH- or _Cs c_ ;

88881.doc 1342330 wherein L 2 and L33 are each independently Η or F. (If not directly measured, the Δ ε value for a single compound can be used as the known concentration in the standard mixture of the standard mixture of the starting mixture (generally Mud KGaA, Darmstadt, ZLI-4792, Germany). The value determined for this single compound (typically 10% by weight) is obtained by extrapolation. Further parameters of the mono-compound can be similarly obtained). Preferably, the component (α) comprises at least one compound of the formula and/or at least one compound of the formula 11: (He (F)f wherein C, d ' e and f are independently of each other, J, J, 2, 3 or 4; R&quot Is a Cl_Cl5 alkyl group which is unsubstituted or mono- or poly-substituted by CN or halogen and wherein one or more Cl groups are independently of each other via -0, -S-, -CH=CH-, C· , -C0-0-, -0 (:·0_ permutation such that the heteroatoms are not adjacent to each other; R is a C2_Cl5 alkenyl group which is unsubstituted or mono- or poly-substituted by CN or halogen and one or more of The CH2 groups may be independently substituted with each other by -0-, -S-, -CH=CH·, -C Ξ C·, -C0···,_0C_0_ such that the heteroatoms are not adjacent to each other; Z and Z are independent of each other. Single button or C-. 88881.doc -16- Another object of the present invention is a dual stable liquid crystal device comprising: _ two external substrates which form a liquid crystal cell together with the frame; _ there is liquid crystal in the liquid crystal cell a composition having an alignment layer on the inside of the outer substrate, such that at least one of the alignment layers includes an alignment grating that allows molecules (compounds) of the liquid crystal composition to adopt at least two different stable states Therefore, the assembly of the electrode structure and the alignment layer is such that switching between the at least two different stable states can be achieved by applying an appropriate electrical signal to the electrode structure; wherein the liquid crystal composition is the liquid crystal combination described above and described later. And including the components (ά) and (β). In particular, the dual stable liquid crystal device is a pole double stable nematic liquid helium device, wherein the electrode structure having an alignment layer on the inside of the outer substrate has at least An alignment layer comprising an alignment grating that allows at least two different steady state states of the compound of the liquid crystal composition (or the guide of the molecule) to have different pretilt angles on the same equidistant azimuthal plane, thus the electrode structure The assembly with the alignment layer enables switching between the at least two different stable states by applying an appropriate electrical signal to the electrode structure. It is to be understood that the subsequent description of the present invention is primarily directed to a pole double stable nematic liquid crystal device. The liquid crystal composition described above is used, but it can be used in other liquid crystal devices such as the above dual-liquid crystal device of the equidistant azimuth dual-state liquid crystal device (As disclosed in WO 92/00546 and WO 95/22077.) Therefore, the detailed description is directed to a pole double stable nematic liquid crystal device, but it can be easily applied to other types of dual stable liquid crystal devices. 8888l.doc 17 1342330 The pole double stable nematic device of the invention and the liquid crystal composition for the pole double: column device show improved parameters 'which makes the parameter operating voltage, operating window, optical response time and especially It should also be noted that, for example, the pure point of the invention is stable to the crucible, the liquid crystal of the H device, and the transparent point of the mouth substance is significantly higher than the transparency of the liquid crystal mixture previously used for the pole double stable nematic device. point. Both the operating power M and the operating window are within the range of dual stable stabilizing devices that can be used with the operating pole.

The liquid crystal cell which is part of the extremely dual stable nematic device of the present invention may be any conventional liquid crystal cell which can be used in a nematic liquid crystal composition to have two different pole double stable states. Two possible steady states are illustrated in Figure 1. The two different pole double stable states are characterized by two different pretilt angles employed by liquid crystal molecules on the same equidistant square plane. The liquid crystal cell comprises a frame and two outer substrates or plates and has an electrode structure having an alignment layer on the inner surface of the substrate. At least one of the alignment layers has a pole alignment grating known to those skilled in the art and is described in the SPIE journals such as W〇97/14990, WO 01/40853, WO 02/08825, and JC Jones. Volume 3955 (2000), 84. The electrode structure and the alignment layer are assembled in the form of (in the case of two stable states) by applying an appropriate electrical signal to the electrode structure, thereby applying the electrical signal to the liquid crystal composition in the liquid crystal cell. Switching from one steady state to another. Conventionally, a single pulse can be used as the appropriate electrical signal. The details are well known to those skilled in the art and are described in W〇97/14990, W0 01/40853, W0 02/08825 and JC J0nes, jr Hughes, A. Graham, P. Brett, GP Bryan-Brown, IDW'OO ( 2000), 301, J. 8S881.doc -18- 1342330 C. Jones et al., SPIE Journal, Vol. 3955 (2000), 84 and EL Wood, P. J. Brett, GP Bryan-Brown, A. Graham, RM Amos, S. Beldon, E. Cubero and JC Jones " Large Area High Resolution Portable ZBD Display, SID 02 Program (2002), 22-25. The substrate relative to the substrate having the grating alignment layer may have a vertical alignment alignment due to suitable surface treatment (see Figure 2a). Switching from a high tilt or vertical alignment state to a low tilt or mixed alignment state due to the application of an electrical pulse. If the liquid crystal cell is placed between the cross-polarizer (45 degrees relative to the grating direction), the switching produces a black-to-white (B_W) change when the vertical alignment state acts as a half-wave plate (<^ When Δη = λ/2), the brightest white state is obtained. This switching mode is called VAN mode. The pole double stable state device using the VAN mode is extremely insensitive to cell gap variations. It requires an additional optical compensator to achieve a wide viewing angle. The second switching mode of the pole double steady state device is referred to as the TN mode (see FIG. 2b): the substrate with respect to the substrate having the grating alignment layer has an alignment layer, typically a rubbed polyimide, which can cause the substrate The plane alignment of the upper liquid crystal molecules. This then causes the liquid crystal director to twist around it perpendicular to the substrate and through the axis of the liquid crystal cell. The application of an electrical pulse now occurs from a low dip or torsional alignment to a high dip or mixed alignment. If the cell is placed between parallel polarizers and utilizes a slightly modified TN 1 "minimum condition (as described above) (this is the reason why the general refractive index of the state is affected), then this switching produces black -to-white (B_W) variation. Due to the high normal incidence contrast ratio, there is no need for an additional optical compensator to achieve a wide viewing angle in the transfer display. Therefore, the technical application of most pole double stable nematic devices And 8888l.doc -19, in other words, the TN mode is better. It is also possible to establish a pole double stable reflective display and even a pole double stable transflective display. For details on the polarizers used, see WO 97 /14990, EL Wood, GP Bryan-Brown, P. Brett, A_Graham, JC Jones and JR Hughes, SID 00 (2000), 124 and EL Wood, P. J. Brett, G. I>.

Bryan-Brown, A. Graham, R. M. Amos, S. Beldon, E. Cubero and J. C. Jones " Large Area High Resolution Portable ZBD Display ", SID 02 Program (2002), 22-25. In the context of the present invention and the compound of the present invention for use in a dual-stabilized liquid crystal device, particularly for a liquid crystal composition t for a pole double stable nematic device, the term ", alkyl" is used in this specification or Where the position outside the patented vehicle is not defined differently, it means a straight-chain and branched hydrocarbon (aliphatic) group containing from 1 to 15 carbon atoms; the hydrocarbon group may be unsubstituted or one or more Independently selected from the group consisting of a substituent of F, Cl, Br, I or CN. The sub-type "alkyl group" containing an aliphatic saturated group may also be referred to as "alkanyl". Further, "burning base" Also means an unsubstituted or similarly substituted hydrocarbon group in which one bite a plurality of CH2 groups via a hydrazine-substituted ("alkoxy","oxyalkyl group), via _s_ ("sulfanyl"), via -CH=CH-substitution ("alkenyl"), substituted (,,alkynyl), via-C0-0- or -0_CO_ (which is not adjacent) Atomic (〇, s)) substitution. Preferably, the alkyl group is a direct or branched saturated hydrocarbon having 1, 2, 3, 4, 5, 6, 7, or 8 carbon atoms which has not been substituted or has been polysubstituted by F. More preferably, the pit pitch refers to methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl tert-butyl, n-pentyl, neopentyl, n-hexyl, n-heptyl-n-octyl ; CF3, cHF2, cH2F; CFzCF3. Preferably, the alkyl group is a linear hydrocarbon group containing up to 8 carbon atoms. 88881.doc •20· 1342330 Since one or more of the Ch2 groups of the alkyl group can be replaced by _〇_ as described above, the term “burning base” also includes "house oxygen" and, oxane "Alkyl group" means a group in which an oxygen atom is directly bonded to a group or ring to be substituted by an alkoxy group, and the alkyl group is as defined above. "Mercaptoalkyl,"alkyl" means methyl, ethyl 'n-propyl, isopropyl, n-butyl, isobutyl, t-butyl, n-pentyl, neopentyl, Is n-hexyl, n-heptyl or n-octyl, and thus the alkyl group is optionally substituted by F. Preferably, the alkyl fluorenyl group is _〇Ch3, _〇c2h5, -0-n-C3H7^-0-n-C4H9^- 〇-t-C4H9 ^ -OCF3 > -OCHF2 ^ -OCHF or -OCHFCHF2. In the present invention, the term "oxyalkyl" includes at least one non-terminal CH.2 group via a ruthenium which does not interact with an oxygen atom. Alternating to the alkyl group, the oxime is not adjacent to the oxygen atom. Preferably, the oxyalkyl group comprises a linear group of the formula CtH2t + 1-0-(CH2)u-, wherein t and u are independently of each other, 2, 3, 4, 5 or 6', especially t is 丨 or 2 and u is an integer from 1 to 6. If one or more Cl groups of the yard group are replaced by sulfur, the "sulfanyl group" is obtained. The sulfanyl group includes at least one terminal or non-terminal CH2 group substituted by s (sulfur) so as not to be adjacent to the sulfur atom. Preferably, the sulfanyl group comprises the formula 0^21+1 winter (〇^2) (1- straight chain group, wherein 1, 2, 3, 4, 5 or 6 and 11 are 〇 1, 2, 3, 4, 5 or 6; especially t is 1 or 2 and u is an integer from 1 to 6. In the present invention, the term '"alkenyl" means that one or more of them are present. Ch=ch-based alkyl. When two -CIi=CH- groups are present, the group may also be referred to as "aldienyl". The alkenyl group may include 2 to 15 carbon atoms and may be a straight chain or a branch. It may be unsubstituted or mono- or polysubstituted by F, C, Br, I or CN; one or more of its CH2 groups may be independent of each other by _〇s_, _c Ξ c_, -c〇 _〇_, -〇C-0~ substitution, and thus the heteroatoms are not adjacent to each other. If the alkenyl CH=CH group 88881.doc -21 - 1342330 is not the terminal CH2=CH group', there are two configurations , ie, the isomer and the z-isomer. Usually, the E-isomer (trans) is preferred. Preferably, the dilute contains 2, 3, 4, 5 6 or 7 carbon atoms and means vinyl, iota-propenyl, 1E-butenyl, 1E-pentenyl, 1E-hexenyl, 1E-heptenyl, 2-propenyl' 2Ε·butene , 2Ε-pentenyl, 2Ε-hexenyl, 2Ε-heptenyl, 3-butenyl, 3Ε-pentenyl, 3Ε-hexenyl, 3Ε-heptenyl, 4-pentenyl, 4Ζ- Hexyl, 4-nonyl-hexenyl, 4-dehexenyl, 5-hexenyl and 6-heptenyl. More preferably, the alkenyl group is an ethylene group, a 1 Ε-propyl group, a 3 fluorene-butenyl group. When one or more CH2 alkyl groups are replaced by _Cs C-, an alkynyl group is obtained. Further or a CH2 hospital group may be substituted by -C0-0- or -0-CO-. : ethoxylated, propyloxy, butyloxy, pentyloxy, hexyloxy, ethoxylated fluorenyl, propyloxymethyl, butyloxy fluorenyl, pentaneoxy Methyl, 2-ethoxymethoxyethyl, 2-propoxycarbonylethyl, 2-butoxyethyl, 2-ethyloxypropyl, 3-propoxypropyl, 4 _Ethyloxybutyl, methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl 'butoxycarbonyl, pentyloxycarbonyl, decyloxycarbonylmethyl, ethoxycarbonylmethyl, propyl Oxycarbonylmethyl, butoxycarbonylmethyl, 2-(methoxycarbonyl)ethyl, 2((ethoxycarbonyl)ethyl, 2-(propoxycarbonyl)ethyl, 3-(methoxy Alkylcarbonyl)propyl, 3-(ethoxycarbonyl)propyl and 4-(methoxycarbonyl)butyl. In the present invention, 'halogen" means F, α, hydrazine and/or work. The liquid crystal composition of the (polar) double stable (nematic) liquid crystal device of the invention contains at least two different components: component (α) and component (magic). The component 〇) contains one or more compounds having a dielectric anisotropy of 25 or more, especially 30 or more. The compound (α) of at least 25% by weight, preferably 3, S8881.doc -22 to 1342330% by weight or more (based on the total weight of the composition) exhibits a dielectric anisotropy Δe of 40 or more. The liquid crystal composition of the pole dual stable nematic device of the present invention should comprise at least 3% by weight (based on the total weight of the composition) of the component (α). Preferably, the liquid crystal composition comprises 35 wt% or more, even more preferably at least 40 wt%, and still more preferably at least 45 wt%, preferably 50 wt% or more of the component (?). The inventors have found that the ingredient (ο;) preferably comprises one or more formulas! A compound or one or more compounds of formula II or one or more compounds of formula I and a compound of formula π (except for other compounds which may be present having the desired dielectric anisotropy). In a preferred embodiment of the invention, component (9) contains at least one formula but no compound of formula II; in another preferred embodiment, component (α) contains at least one compound of formula II but no compound of formula I. If the component (α) contains at least one compound of the formula J, the compound of the formula I is present in a total amount of at least 5% by weight, preferably at least 1% by weight, more preferably at least 15% by weight or more. If the component (?) contains a compound of the formula, the compound of the formula II may be present in an amount of from about 5 to about 3% by weight, preferably from 8 to 25% by weight, more preferably from 10 to 20% by weight. However, if the ingredient (α) contains a compound of the formula II above, the total amount of the compound is in the range of from about 5 to about 55% by weight, preferably from about 8 to about 35 parts by weight. /. Preferably, it is from about 9 to about 25 weights 0/0. 88S81.doc

丄 CM

η • 23- 1342330 For compounds of formula I, C and d can be independently of each other, 1、, 1,? Ζ, 3 or 4, preferably 0, 1 or 2; it means that the benzene rings of the preferred formula are each unsubstituted or mono- or di-substituted by fluorine. If such a F substituent is present, it may be substituted at the acyclic ring and/or independently of each other. Better

(He is, a "^L12, and Lll&Ll2 are independent of each other or F. Further, z11 can be a single bond (so CN is directly bonded to the benzene ring) or c_c triple bond thus forming a stupid ring-C ^C_CN substituent. Preferably, zll is a single bond. The preferred formula Ι φ is the following compound:

S8S8tdoc -24- 1342330

88881.doc •25-1342330 and R is as defined above. Preferably, 1111 of the formulae 1 and 18 to 1] is a linear alkyl group, particularly an alkane group having 1, 2, 3, 4, 5 or 6 carbon atoms. A highly preferred compound is a compound of the formula 而 1 and n = 1, 2, 3, 4, 5 or 6.

Particularly preferred examples of the compound of the formula j which are present alone or in combination with each other in the component (α) are the following compounds of the formulae II to 13:

Preferably, the liquid crystal composition has a mixture of all three compounds Π, Ι2 & Ι3. For example, Compound II exhibits a dielectric anisotropy Δ£ of 37 5 and Compound 13 has a Δ ε of 36.0. The compounds of formula II 'e and f' are independently 〇, 1, 2, 3 or 4, preferably 0, 丨 or 2; which means that the abbreviated ring of each of the formulas may be unsubstituted or fluorinated. - or two-substituted. If the F substituent is present, it can be right-stringed

It is a single bond (so CN is directly bonded to the benzene ring) or c_c double bond thus forming a -C=C-CN substituent of the benzene ring S8881.doc -26- 1342330. Preferably, Z21 is a single bond. Preferred compounds of formula II are the following compounds:

IIA

IIB

IIH 88881.doc -27 1342330

R21 is as defined above. Preferably, the formula H&IIA to IIM is a linear alkenyl group which particularly contains 2, 3, 4, 5 or 6 carbon atoms and preferably contains a terminal c=C double bond. A highly preferred compound is a compound of formula IIB1 and n = 2, 3, 4, 5 is 6 〇

IIB1 is present alone or in combination with each other in the composition (a good example of a substance in the case of the following formula m to „4 compound··

F 111 II2 -28 1342330

The most preferred compound of formula II is a compound 114 exhibiting a dielectric anisotropy Δ ε of 59.5. Regarding the component (none), the amount of the component present in the liquid crystal composition t in the pole double stable nematic device of the present invention is at least 5% by weight or more. Obviously, the composition (jS) is necessary for the high transparency of the liquid crystal mixture used in the pole double stable nematic device. Ingredient (/3) includes Formula III and / or Formula and V and / or Formula VI and / or Formula VII. / or

III

R6'-

R62

V VI VII and a, b, R31, R32, R41, R42, R51, R52, R61, K, R71, 88881.doc -29- 1342330

Q 7 2 Τ 3 1 4 1 72 A T'V R , L , Z and VIII , 8 , 〇 , 1 ) , £ and 17 are as defined above. For formula III, preferably a is i. The preferred formula is a gas.

R31 and R32 are as defined above. Preferably, in the formula <IIIAiIIIG, r; m and R32 are each independently a linear alkyl group, more preferably a linear alkane or alkenyl group having 2, 3, 4, 5 or 6 carbon atoms, especially A linear hydrocarbon group having 2 to 6 carbon atoms, a being 1 and L31 being hydrazine or F (for hydrazine). Highly preferred compounds are of formula IIID and anthraquinone compounds. A particularly preferred example is a compound of the formula ΠΙ1 to ΙΙΙ6: 888$ I.doc -30· 1342330

The compound of the formula 111 is a compound of the formula ΠΙ2, III4 and III6, and preferably 兮 The liquid crystal composition contains a mixture of the two compounds of the right- 。. The invention is somewhat specific to you. In the middle of the formula III, a is 〇. Thus, the preferred compound is of the formula:

R1 and R32, as defined above, are read as straight-line (tetra)-based, straight-chain hydrocarbon groups or counties containing 2, 3, 4, 5 or 6 carbon atoms, especially containing 88881.doc -31, 1342330 'R31 A straight-chain smoky group of 2 to 6 carbon atoms of n-propyl or n-pentyl. In particular, R32 is an ethyl group. For the compound of formula IV, preferred compounds are those wherein 1? is a compound of formula VIII and ivb and a compound of formula IVC and IVD wherein b is 0:

R42 R42

IVA

IVB

IVC

IVD and R, R42 and Z41 are as defined above; Z41 is preferably _CO_〇- or -OCH2. in the case of formula IVD. R41 and R42 are each independently a linear alkyl group, more preferably a linear alkane or alkenyl group having 2, 3, 4, 5 or 6 carbon atoms, particularly a linear alkane having 2 to 6 carbon atoms. base. The compound of formula IVB is more preferred. Particularly preferred examples of formula IV are compounds of formula IV1 to IV3 and compounds of formula IV4 & IV5 and formulas IV6 to IV8:

BBSgl.doc •32- 1342330

IV4 IV5 IV6 IV7 IV8 It is particularly preferred that the liquid crystal composition contains a mixture of the compounds 丨vb and ιν3. a straight-chain alkylene group having a linear alkyl group, preferably a 2, 3, 4, 5 or 6 anti-atom, especially a direct-bonded tobacco base having 2 to 6 carbon atoms. And R is a linear compound, or more preferably an alkoxy group having 1, 2, 3 or 4 carbon atoms. A particularly preferred example is a compound of the formula v! to v6:

88881.doc -33· 1342330 c„h2

V5 V6 wherein Π is an integer from 1 to 6, preferably 2, 3 or 4, especially 3. Preferably, the compound is a compound of the formula V2, V4 and V6 wherein n = 3 (an n-propyl substituent is obtained). Preferably, the liquid crystal composition contains a mixture of all three compounds V2, V4 and V6. Preferably, in the formula VI, R61 is a linear alkyl group, more preferably a linear alkenyl group having 2, 3, 4 or 5 carbon atoms, and R62 is a linear alkane group or an alkoxy group, both of which contain 1, 2, 3, 4 or 5 carbon atoms (in the formula VIA or VIB, 11 = 1, 2, 3, 4, 5 and m = 1, 2, 3, 4, 5).

Preferred compounds of formula VI are the compounds of formula VII to VI4:

VI2 88881.doc -34- 11342330 ί

Ο

Ο VI3 VI4 is a compound of formula VII, VI3 and VI4. It may be used alone or more preferably as a mixture of two or three compounds. For a compound of formula VII, the specific compound is of the formula:

VIIA VI old

VIIC VIID and R71 and R72 are as defined above. Preferably, R7i and r72 are a linear alkyl group, more preferably an alkane group having 1, 2, 3, 4, 5 or 6 carbon atoms. Preferred compounds of formula VII are:

VIIC1 V11D1 and m and m are independent of each other, 1, 2, 3, 4, 5 or 6. The best compound of formula VII 88881 doc -35- 1342330 Examples are:

The vin VII2 VII3 VII4 component (/?) is used in a liquid crystal composition for use in the pole double stable nematic device of the present invention in an amount of 5% by weight or more. When the component (α) comprises at least one compound of the formula II, it is preferred that the liquid crystal composition comprises 8% by weight or more of the component (/5). When the component (9) is free of the compound of the formula I, the component is at least 10% by weight (perfect is better. In some specific examples of the invention, the total amount of the component (/3) is 15 or 20% by weight or more (/5) It is highly preferred. In a specific embodiment of the present invention, the component (/5) may contain only one compound of the formula III or IV or V or VI or VII. It may also contain two of the formulae III to VII. Or one or more compounds of three or more kinds, which may contain equal or different amounts of each compound used. The preferred component (/3) contains one or two of formulas III, IV, V, VI or VII or a plurality of compounds. If two compounds of the formulae III to VII are contained, there may be any combination, that is, III + IV or III + V or III + VI or III + VII or IV + V or IV + VI or IV + VII Or V+VI or V+VII or VI + VII; the two types of compounds may be used in equal amounts, or one type of compound may be used in excess of the other, for example, in a ratio of 2: 1. It is preferred to use equal amounts of the two types of compounds. When the component (/3) contains two kinds of formulas 88VIII.doc-36-1342330 of the formula III 'IV, V, VI and VII, one of the preferred compounds is a formula. Therefore, the preferred composition is III + IV, III + V, ΠΙ + νι & Ι π + νιι. When the composition includes at least the compound of the formula 11, the preferred component (|8) includes the formula III, IV, V, VI and Two compounds of VII are known. However, it is understood that the compound other than the formula J and the formula π may have only two dielectric anisotropies Δ ε and do not impair the parameters listed above. Accordingly, it is preferred that the component (α) of the liquid crystal composition used in the pole double stable nematic device of the present invention also includes - or particularly a plurality of compounds of the formula ν (1):

Wherein g and h are independently of each other, 1、, 1, 2, 3 or 4; is Ci-c, 5 alkyl 'which is unsubstituted or mono- or poly-substituted by CN or halogen, and wherein _ or more eh groups The substitutions _〇_, -s-, -c^c-, <〇_〇_, _〇c 〇 may be independent of each other such that the heteroatoms 81 are not adjacent (which means that R81 does not include any alkenyl groups) ; Z81 is a single key or -C^C-. t Regarding the compound of the formula VHI, g and h may independently be 0, i, 2, 3 or 4, 1 or 2; it means that the stupid ring of the preferred formula VIU may be unsubstituted or gas-single- or two Take A. If a nail substituent is present, it can be substituted anywhere in the ring S8881 .doc -37-1342330. Preferably, 1"/ and/or each other is independently .91 /ΡΊ \ can be a single bond (so CN is directly bonded to the benzene ring) or a C-C triple bond thereby forming a benzene ring-CeC-CN substituent. Preferably, Z81 is a single bond. Preferred compounds of formula VIII are the following compounds:

And L (F)h " and! ^82 are independent of each other or F. Furthermore Ζ 8 1

VIIIA VII old

VIIIC

VIIID

VIIIE

VIIIF 88881.doc -38- 1342330

A linear alkyl group, especially a linear alkane group having 1, 2, 3, 4, 5, 6, 7, or 8 carbon atoms. Highly preferred compounds are the compounds of the formulae VIIIA1 and VIIIB 1 and 11 = Bu 2, 3, 4, 5 or 6, wherein the compound of the formula 八111 VIII is most preferred.

V1I1A1 VIIIB1 The best compound of the formula νπι is a compound of the formula vmi to vm6: 88881.doc -39- 1342330

F

Vim

VIII2

VIII3

VIII4 VIII5 VIII6 wherein the compounds of the formula vnn (having dielectric anisotropy "53 7), νιπ2, vm3 (^=44.9) and νπΐ4 (Δ(tetra) 3 〇) are optimal. If present, the pole of the invention is double The total amount of the compound of formula VIII in the liquid crystal composition stabilized in the twinning device may be about 10% by weight or more (but may also be present in minor amounts), preferably 20% by weight or more, more preferably at about 25 In the range of up to 6% by weight, more preferably in the range of from about 35 to about 55 weights 〇/〇. When a mixture is used, different compounds of the formula νπι can be contained in the component (α) in almost equal amounts. For example, if used The compound of the formulae VIII1 to VIII4, which may contain a ratio. 8888l.doc -40 - 1342330 In another preferred embodiment of the present invention, the component (α) of the liquid crystal composition used in the pole double stable nematic device includes At least one compound of formula IX:

R

Z-CN

Wherein IX is 0 or 1; R91 is a Ci-Cu alkyl group which is unsubstituted or mono- or poly-substituted by CN or halogen and wherein one or more CH 2 groups are via -Ο-, -S-, - CH=CH-, -(: three C-, -CO-0-, -0C-0- substitutions such that the heteroatoms are not adjacent to each other; Ζ91&ζ92 are independent of each other as a single bond or -CEC-;

Among them, L91, L92, L93 and L94 are independent of each other or F. 88881.doc -41 · 1342330 The preferred class of compounds encompassed by formula IX are compounds of formula IXA to IXE wherein Z91 is a single bond: L93

Z-CN

IXA

IXB

IXC

IXD

IXE: a straight-chain alkane-based, preferably or a single-chain, or S2 3, 4, 5 or 6 carbon atoms, or preferably a single Key; and. , ” and π are two F and L and L, preferably H. The preferred formula ΙχΑ to (10) compound is: 88881.doc -42· 1342330

IXA1 IXA2 IXA3 IXB1 IXB2 IXB3 IXC1 IXC2 IXC3 88881 .doc -43 1342330

F

IXD1 IXD2

IXE1 IXE2 where R91 is as defined above. Some specific examples of compounds of formula IX are:

F If the compounds are present in component (α), the total amount may range from about 5 to about 45 weight percent. It is preferably used in the liquid crystal composition of the present invention to contain only one type of hydrazine to hydrazine compound. 88881.doc -44- 1342330 In another preferred embodiment of the present invention, the liquid crystal composition for the dual steady state liquid helium device of the present invention and especially for the pole double stable nematic device further comprises 3% by weight Or a component (γ) having one or more compounds having an optical anisotropy Δη of at least 0.20. It has been found that the use of the component (?) lowers the operating voltage V?Pt of the liquid crystal composition. In general, the component (?) may include any (intermediate) compound which exhibits at least 〇?2??? of the parameters which are of particular importance for the pole-double stable nematic liquid crystal device. Preferred components include diphenylacetylene having a Δη of at least 0.20, especially at least one diphenylacetylene compound of the formula:

Wherein k is 〇, .1, 2'3 or 4; R and 尺1<>2 are each independently qc,5 alkyl, which is unsubstituted or substituted by CN or halogen mono- or poly- and one of Or a plurality of CH 2 groups may be replaced by -Ο-, -s-, -CH = CH-, -CE C-, -CO-O-, -〇C_〇_ such that the heteroatoms are not adjacent to each other;

Particularly preferred compound of formula XA: 88S81.doc -45- 丄342330

its

Wherein η and m are independently of each other i'2, 3, 4, 5 or 6 and ^ is 〇, 1 or preferably a preferred example is IXA1 and η is 2, 3 or 4 and ni is 1, 2 3, 4 or 5 .

ΙΧΑ1 Which is best for compounds IXAla and IXAlb:

F

F F

F IXAla IXAlb If component (γ) is present, it is present in an amount of at least 3% by weight and more preferably at least 5% by weight. The liquid crystal composition used in the dual steady state liquid crystal device of the present invention and especially for the pole double stable nematic liquid crystal device may include other materials for adjusting the properties of the composition if necessary. For example, some of these materials can be used to adjust the viscosity of the liquid crystal composition. In some embodiments, the liquid crystal composition for use in the pole dual stable nematic device of the present invention comprises at least one compound of formula XI and/or at least one compound of formula XII and/or at least one formula 88881.doc-46- XI1342330 compound and / or at least - a compound of formula XIV

Y 111 132

XII

R

XIII

XIV R111 and R142 are independently of each other as C2_Ci5 alkenyl (3) or dentate mono- or poly-substituted and one or more of them are called base = this independent m, -CH=CH_, uc_, c〇〇·-OC-0-substitution , such that the heteroatoms are not adjacent to each other; R131, R"2 and R141 are each independently a Ci_Ci5 alkyl group, which is unsubstituted or mono- or poly-substituted by CN or a functional group and wherein one or more CH2 groups are each other Independently 〇, _s, = dτ, three c, -C0-0-, _0C_0-, such that the heteroatoms are not adjacent to each other; 122 R is a Cl-Cl5 alkyl group which is unsubstituted or mono- or poly-halogenated Substituting and wherein one or more of the CH2 groups may be independently substituted with each other via _〇·, _s, -CH=CH-, -C=C-, _Co_〇·, _〇c_〇_ such that the heteroatoms are not Adjacent; Y is a Ci/Ci5 alkane or C2-cls alkenyl group which is independently mono- or poly-substituted by halogen, or a Ci_Ci5 which is mono- or poly-substituted by halogen, which is unsubstituted or

R 121 8888l.doc • 47- 1342330 alkoxy; L111 and L112 are each independently Η or F; and are independent of each other'

Liquid Crystal Compositions The exact nature and amount of such compounds will depend on the particular mixture and the desired effect and can be readily selected by those skilled in the art. Preferred compounds of formula XI are hydrazine or hydrazine compounds:

CnH2

XIA

A

XIB wherein η is 2, 3, 4, 5 or 6 and Y111 is selected from the group consisting of F, Cl, CF3 and OCF3. The particularly preferred compound of formula XI is the following compound:

X11

F F

XI2

F

XI3 XI4 88881.doc -48- 1342330 The best compound of the formula 为 is the compound xii. Preferred compounds of formula XII are compounds of formula XI, XIIB ' XIIC, XIID, XIIE and XIIF: C, H2n,

OC„H -o CmH2m+, 2m+l

CnH2n.f

C〇H2n

<y<y 2m+1 〇CmH2m+1 Ί·

Wherein n is 1, 2, 3, 4, 5 or 6 and m is 1, 2. The specific examples of the compound are the following compounds:

X1IA XIIB XIIC.. XIID XIIE XIIF4, 5 or 6. Formula XII XII1 XII2 88S81.doc -49- 1342330

XII3 XII4 XII5 XII6 X1I7 XII8 XII9 ΧΙΜΟ XII11 The preferred compound of formula xiii is a compound of formula XIIIA or 乂11118. -50- 888Sl.doc 1342330

CnH

CnH2n+ α-Qt XII1A XI is old and n is 1, 2, 3, 4, 5, 6, 7, or 8 and m is 1, 2, 3, 4, 5 or 6. A particularly preferred example of a compound of formula XIII is the following compound:

XIII1 XIII2 XIII3 XIII4 XIII5 XIII6 The preferred compound of formula XIV is a compound of formula XIVA: ^η^2η+ί ^0~CmH2n

XIVA 88881.doc -51 - 1342330 and η is 1, 2, fly, j 4, 5' 6, 7 or 8 and m is 2, 3, 4 xiv compounds Specific examples are the following compounds:

XIV1 XIV2 XIV3 XIV4 XIV5 The best compound of formula XIV is compound XIV2. The liquid crystal composition for a dual-state liquid crystal device according to the present invention may also include an intermediate type substance having a mussel dielectric anisotropy Δ ε of about 8 to 10 or more, for example, or a compound of the formula xv and/or a Or a plurality of compounds of the formula XVI, preferably 30% by weight of Xia Shangda, more preferably about 2% by weight:

F

Wherein R and 11 are each independently a Ci-Cis alkyl group which is unsubstituted or mono- or poly-substituted by CN or halogen and wherein one or more CH 2 groups are 8888l.doc -52- this independent via-0 ', -s-, -CH=CH-, -CE c-, -CO-0--oc-o gastric replacement' makes the heteroatoms not adjacent to each other; γ and Ym are independent of each other, F, C - or poly-substituted dQ smoulding' or a mono- or poly-substituted C1_C15 alkoxy group; L 31 and L161 are independently η or f; and 2 is -C0-0-, CH20 or cf2〇 . The car is also a good compound for the XVA 'XVB and XVIA:

F

XVA

XVB

F F

CnH2n"

XVIA and η is 丨, 2, 3, 4, 5, 6, or 7 in the three equations. These materials can simultaneously affect the operating voltage and operating window required for the liquid crystal composition of the pole double stable nematic device of the present invention. The liquid crystal composition for a pole double stable nematic device according to the present invention may further comprise - or a plurality of intermediate materials of the following formula XVIISXXII. The nature and amount of such compounds in the liquid crystal composition will depend on the particular mixture and the desired effect and can be readily selected by those skilled in the art. 8S881.doc -53- XVII 172 1342330

XVIII

XIX

XX

XXI

XXII in its R17

R 172

R 181 R "2, r20丨, r2" and r221 are independent of each other

R 19 alkyl group which is unsubstituted or single or poly-substituted by CN or a functional group and wherein one or more CH 2 groups may be independently of each other via _〇_, _s, -CH=CH-, r 〇弋= C-, -C0-0_, _〇C-〇·substituting heteroatoms; both are not adjacent; Ci-C〗 <; Detecting soil, which is unsubstituted or passed through CN or halogen cover - Or multiple-substituted and singly eight τ one or more ch2 groups can be independent of each other 纽-0-, Γ = C, 〇〇-〇-, -OC-O- permutation, so that 8888 丨.d〇c -54· 1911342330 Heteroatoms are not adjacent to each other (which means that R191 does not represent an alkenyl group); L192, L201, L2〇2, L203, [204, [211, l212, [(1), L214, L215, L216, L221, L222, L223 and L224 are independent of each other as H or F;

Ym, γ2〇丨, γ2丨丨, and γη丨 are independently of each other, F, α, and C-—C, 5-alkane or (2-C15 alkenyl) or Halogen mono- or poly-substituted (^-(:^ alkoxy. The preferred compound of formula XVII is a compound of formula XVIIA to XVIIC:

CnH2

CpH2p*1

CqH

XVIIA XVIIB XVIIC and dm are independently of each other, 2, 3, 4, 5, 6 or 7 and independently of each other, 3 4 5 6 or 7 is more preferably a compound of the formula χνιι a, and n is 2, 3, 4, 5' The claws and the claws are eight and the other, and the formulas are independent of each other, 2, 3, 4 or 5; A preferred compound of formula XVm is formula XVIIIA:

C„H

CPH2M

XVIIIA and η are 1, 2, 3, 4, 5 are compounds of the formula XVIIIA, 6 or 7 and p is 2' 3, 4, 5, 6 or 7. More preferably, n A 1, 1 horse 2, 3, 4 or 5 and p are 2, 3, 4 and 5; 88881.doc -55, 1342330 particularly good CnH2n+1 is methyl, ethyl or n-propyl and cH ρ Γ 12ρ-ι is -ch2-ch2-ch=ch2 or -CH2-CH2-CH=CH-CH3 group, the latter preferably c = c double bond is E-configuration. Preferred compounds of formula XIX are of formula XIXA and XIXB:

F

XIXA

XIXB and η is 1, 2, 3, 4, 5, 6 or 7 and Y191 is f, ci, (^3 or 〇CF" more preferably a compound of the formula XIXB and η is 2, 3, 4, 5, 6 or 7 and Y191 are f. The preferred compound of formula XX is formula ΧΧΑ to XXG:

F F

F F 88881.doc

Γ2〇 ΧΧΒ

XXC

XXD ΧΧΕ 1342330

F F

Wherein n is 1, 2, 3, 4, 5, 6 or 7 and Y201 is F, Cl is more preferably a compound of the formula XXB, XXC and XXD and n is 2 and Y2G1 is F. Preferred compounds of formula XXI are of formula XXIA to XXIJ: XXF XXG CF3 or OCF3. 3, 4, 5, 6 or 7

V 211 γ2”

CnH2l :n+1

211 F F

XXIA XXIB XXIC XXID XXIE 88881.doc -57- 1342330

F P F

XXIF

F F

Y21 y211

XXIG

XXIH XXIJ and n is 1 '2, 3, 4, 5, ό or 7 and Y211 is F, Cl, CF3 or 〇CF3. More preferably, it is a compound of the formula XXID and n is 2, 3, 4, 5, 6 or 7 and Y2丨1 is p.

Preferred compounds of formula XXII are formula or XXIIB: F F

XXIIA XXI is originally F, Cl, CF3 or 〇CF3, 4, 5, 或 or 7 and 丫221 is 1? and η is 1, 2, 3, 4, 5, 6 or 7 and Y is more preferably a ruthenium compound Further, η is 2, and it is preferred that the liquid crystal composition used in the present invention is a nematic liquid crystal composition. It will be apparent to those skilled in the art that liquid crystal compositions for use in accordance with the present invention may include additional (intermediate) compounds in addition to those compounds described in more detail in this specification. A wide variety of intervening compounds can be used as long as their 88881.doc -58-1342330 does not detract from the important parameters of the dual stable liquid crystal composition used in accordance with the present invention. A further object of the present invention is a liquid crystal medium comprising: at least one compound of the formula I as defined above; and at least one of the above formulae and/or at least one compound of the formula 1 and/or at least one compound of the formula V and/or At least one compound of the formula VI and/or at least one compound of the formula VII. The "Bei Shi case includes at least one compound of formula VIII as defined above. Still another object of the present invention is a liquid crystal medium comprising: the above definition: at least one compound of the formula π; and at least one of the above formulas and/or at least one compound of the formula IV and/or at least a compound of the formula And/or at least one compound of the formula VI and/or at least one compound of the formula VII. The "quality of matter includes at least one compound of formula VIII as defined above. The liquid crystal composition for use in the pole double stable nematic device of the present invention also contains the optically active component α) as a dopant in an amount of from 0 to 3% by weight. «Hai versus dry dopants can be used in the τ_ equation to remove the reverse torsion region. The compound of the j type is suitable as the component (component of (1), and all of the substances which are exemplified by the cockroach are cholesteryl decanoic acid vinegar ((3)), m s S 〇 H ^ S - 2 〇 H ^CB15(Merck KGaA, Darmstadt, #1) 〇0 S-811 may be a preferred dopant, but the specific choice of dopant is not important: the liquid crystal composition of the pole double stable nematic device of the present invention Usable or a plurality of light stabilizers and/or additives such as those known in the art 88881.doc -59 - 1342330 chromatic dyes. The liquid crystal composition of the double t-state liquid crystal device makes all the compounds used commercially available or can be easily borrowed. Known methods and prepared as described in the Organic Synthesis Standards Reference, such as H〇uben_Weyl,

Ge〇rg-Thieme-Verlag, Stuttgart. The liquid crystal composition will be prepared by applying standard methods and techniques. Typically, the required minor component will be dissolved in the main component, typically at elevated temperatures. Alternatively, a solution in an organic solvent such as propylene glycol, propylene or methanol may be mixed and then the solvent may be removed by, for example, distillation. Similarly, the fabrication of the dual stable helium device of the present invention will be governed by standard techniques known in the art. In the present specification and the following examples, the disclosed intervening compound structure is described using the first word (Curry name). The head word can be converted into a chemical formula according to Tables 8 and 8, in which the residue CnH2n+i&CmH2m+ i is a linear alkyl group having η and 111 carbon atoms, respectively. The alkenyl group has a trans configuration. It can be self-clarified according to the number in Table 8. In the table, only the first word of the parent compound structure is provided. The prefix of the parent compound structure is generally separated by a hyphen (1). The numbers of the substituents R1, R2, 匕1 and L2 are as follows: L2 R^L1, R1 r2 L2 number

η CnHwi nm CnH2n+i nOm CnH2n+l nF nN.F CnH2n+i nN.F.F CnH2rvM

CN H 〇mH2m+1 H 〇CmH2m+i H F H CN F CN F Η Η Η Η Η

F 88881.doc -60- 1342330 Table A:

R

R2 PTP

R

CPTP

ME

CCPC L1

PCH

R1 —<^T^>-CQ2~(^~〇y- R2 ^L2 D

HD

OS

BCH 88881.doc -61 - 1342330 Table B:

CP-nm

CnH2n+1

F

CP-nmF

CCP-Vn-m 88881.doc -62- 1342330

CCP-V-m

PZU-V2-N

PYP-nF PTP-n(0)m

CnH2n+1

F PPTUI-n-m

〇-CmH 2m+1 CVCP-V-Om

CnH2n+1

〇-C^H 2m+1 CVCP-nV-Om

CmH2l m+1

PYP-n

(〇)CmH 2m+1 8888l.doc -63- 1342330

F

F PCH-nN.F.F

CnH2n+1 -^H^C02—(〇)CmH2m+1 D-n(0)m

CGU-n-F

BCH-nRF-F CnH2n+1

CCZU-n-F

DU-nN CDU-nF 88881.doc 64- 1342330 Table C: Table C shows the dopant (component (f)) present in the liquid crystal composition of the present invention for a pole double stable state nematic device, as the case may be. .

0 >-CN C 15 CB 15 CH, c5h13-ch-o-\ ο

〇 c5h” CM 21 .0. csh13〇一< 〇 〇-< 0

〇 0-CH-CaH CH, 13 c3h7

Oy-ch2-ch-c2h5 ch3

CM 45

8888l.doc -65- 1342330

F F

R/S-4011 o 〇 R/S-5011

8888l.doc -66- 1342330 Table D: Table D shows the stabilizers present in the liquid crystal composition of the present invention for the pole double stable state nematic device, as the case may be.

S8881.doc -67- 1342330

88881.doc -68- 1342330

8888l.doc -69 1342330

88881.doc -70- 1342330

The percentages provided herein are % by weight and generally relative to the total amount of the composition or mixture unless otherwise indicated. The temperature is celsius rc) unless otherwise specified. τ means the transparent point when the column medium becomes isotropic. For optical anisotropy (birefringence) (at 589 nm, 2 〇. Δ Δ ε means dielectric omnidirectional $ (at 1 kHz '赃). Κι is the slope elastic constant and K^f elastic constant, two The PN count is used. The photoelectric data has been measured in the VAN pole double stable nematic liquid crystal cell; t. S has otherwise described, these measurements are entered into Z in 2 generations. It is a switching electric field Elc@ derived from correction. (10) In the 25t: in the pole double-stability test state liquid crystal cell, with a true liquid crystal of about 2. 8 to about 5 micrometers d '100 ... pulse) by V ° pt = ELc@ioo«s. dopt (and ~(micrometer) is the corrected operating voltage v AV ju. ^ ° } *叩'', sub-BW-switching and inverse switching 4又 for ^3/(2如), 'again=555 nm) The correction operation at the time of μ pulse is (in v); it is switched from the experimental electric field window (calculated at 25〇c·μμ 88881 .d〇c -71 . 1342330. Optical response time τ_(millisecond and τ is the experiment) The response time, such as the above pulse, multiplied by the above-defined dopt) is calculated from ταρ£=τ . , 疋 and d are experimental liquid crystal cell gaps. The following examples should further illustrate the secret β ^ ^ This patent month and scope of the present invention not to limit its scope. EXAMPLES: An individual sample of the appropriate weight (weight/weight percentage) was weighed to prepare a test sample σ port. The sample αο then homogenizes and mixes well in the same direction. = The compound is then oxidized with a given concentration _ mixing (4) (G2 micro-magic to just leave the liquid crystal mixed with material. For example, Merck Handbook "Liquid Crystal Physical Properties - Description of Manufacturing Method", W. Becker, ed. (1 998) The determination of nematicity to isotropy/m (or transparent point, Tni), dielectric anisotropy (□ e), birefringence (mouth), bevel and bending elastic constant ( Κι&κ3) and rotational viscosity (γι). The value of a single compound is determined from the known concentration in a standard primary mixture (the initial mixture value is also known) (typically 10% by weight of the single compound) Equivalent extrapolation. The photoelectric performance of each mixture in a pole double stable nematic device is determined using a simple experimental setup and a VAN type test cell. This requires a transfer mode microscope with an illuminator connected to the oscilloscope. This can be traced through the cross-polarizer. The test cell is mounted on a heating table under the microscope to measure at 25 ° C. Bipolar electrical pulses (with varying persistence and voltage) are used to ensure application to The helmet on the LCD The dc voltage. Therefore, the trailing edge of each pulse (and therefore its polarity) determines the final switching state (depending on persistence and voltage). Two signal generators are required to ensure that the initial state of the correction is the first choice, The first signal is limited to Ί2·88881.doc 1342330 The second signal (with appropriate phase difference). The two signals increase the amplitude by connecting the output of the signal generator to the test liquid crystal cell through the amplifier and the B_W transition. Lu's measurement of 10 and 90% of the change and the opposite 9〇 and 1% of the transfer of the required voltage to measure the pulse persistence. For the WB transition, only 90 and 1% of the pulse persistence is measured. Passing the voltage required for the change. Once the 0 and 100% transfer values are known (ie, black and white), the values are set on the oscilloscope and can also be used to determine the optical response time of the transition (right 10 and 90% transfer change). VAN type test cell in the transfer mode and in the cross polarizer, use the cell gap. The old type is 3 m. Due to changing the thickness of the cell and the different mixture ^ The resistance Not optimal but without importance, because of low contrast., Drop 888S1 .doc -73- Ϊ342330 Example 1

Amount (wt%) Tni (°C) 92.4 ME2N.F 12 Δε 43.7 ME3N.F 12 Δη 0.1428 ME4N.F 12 Κι (ρΝ) 7.6 ME5N.F 12 Κ3 (ΡΝ) 22.5 HP-3N.F 5 V〇Dt (V) 11.5 HP-4N.F 5 Δν〇〇, (V) 7.3 HP-5N.F 5 t〇pt (ms) 55 CC-5-V 10 γ1 (mPa.s) 448 CCG-VF 15 CCPC-33 4 CCPC-34 4 CCPC-35 a 4 Total 100 I Example 2 Compound amount (Wt0/o) Tn, (°C) 82.6 ME2N.F 12 Δε 43.4 ME3N.F 12 Δη 0.1465 ME4N.F 12 Κι (pN) 7.8 ME5N.F 12 K3 (pN) 17.2 HP-3N.F 5 V〇Dt (V) 14.9 HP-4N.F - 5 AV〇Dt (V) 9.6 HP-5N.F 5 x〇〇t (nis) 38 CC-5-V 16 CCG-VF 10 CCPC-33 3 CCPC-34 3 CCPC-35 2 PPTUI-3-2 3 Total 100 88881.doc -74- [1342330 Example 3 Compound Quantity (wt%) Tn, (°C) 92.3 ME2N.F 7 Δε 43.1 ME3N.F 6.5 Δη 0.1402 ME4N.F 6.5 Κ, (ρΝ) 8.3 HP-3N.F 5 Κ3 (ΡΝ) 14.1 HP-4N.F 4.5 V〇〇t (V) 14.5 HP-5N.F 4.5 AVont (V) 4.7 CC-5-V 20 T〇〇t (ms) 45 CCG-VF 16 CCPC-33 3 CCPC-34 3 CCPC-35 3 PZU-V2-N . 15 PPTUI-3-2 6 Total 100 Example 4 • Amount (wt%) Tni (°C) 97.5 ME2N.F 12 Δε 39.1 ME3N.F 10 Δη 0.1454 ME4N.F 4 Κι (pN) 8.4 ME5N.F 4 K3 (PN) 19.6 HP-3N.F 6 Voot ( V) 18.0 HP-4N.F 6 AVo0, (V) 14.9 HP-5N.F 6 T〇〇t (ms) 67 CCG-VF 8 CCPC-33 5 CCPC-34 5 CCPC-35 5 PDX-3 12 PDX -4 9 PDX-5 8 Total 100 88881.doc -75- 1342330 Example 5 Example quantity (wt%} Tn, (°C) 88.9 ME2N.F 6 Δε 38.4 ME3N.F 6 Δη 0.1462 ME4N.F 5 κ, ( ρΝ) 7.8 ME5N.F 5 Κ3(ρΝ) 16.7 HP-3N.F 4 Vent (V) 10.4 HP-4N.F 4 Δνηη, (V) 1.1 HP-5N.F 4 T〇Dt (mS) 32 CC- 5-V 10 CCG-VF 16 CCPC-33 4 CCPC-34 4 CCPC-35 4 PZU-V2-N 10 PPTUI-3-2 8 PCH-3N.FF 10 Total 100 88881.doc 76- 1342330 Example 6 Compound Amount (wt%) Tni (°C) 88.7 ME2N.F 10 Δε 44.2 ME3N.F 10 Δη 0.1709 ME4N.F 10 Κ, (ρΝ) 9.4 ME5N.F 10 Κ3 (ΡΝ) 18.2 PZU-V2-N 10 V〇Dt (V) 11.6 CPTP-301 5 AV〇Dt (V) 9.3 CPTP-302 5 T〇Dt (ms) 36 CPTP-303 5 D-301 5 D-302 5 D-401 5 D-402 A 5 CBC-33F 5 CBC-53F 5 CB C-55F 5 Total 100 Example 7 Compound amount (wt°/. } TN. (°C) 91.6 ME2N.F 10 Δε 43.3 ME3N.F 10 Δη 0.155 ME4N.F _ 10 Κι (pN) 9.9 ME5N.F 10 K3 (PN) 16.5 PZU-V2-N 10 V〇〇t ( V) 11.0 CPTP-301 5 △Vnot (V) 5.1 CPTP-302 5 x〇〇t (ms) 20 CPTP-303 5 γι (mPa.s) 319 CC-5-V 20 CCPC-33 5 CCPC-34 5 CCPC-35 5 Total 100 88881.doc -77- 1342330 Example 8 Compound amount (wt%) Tni (°C) 91.3 ME2N.F 10 Δε 46.7 ME3N.F 10 Δη 0.2077 ME4N.F 10 Κι (ρΝ) 11.1 ME5N. F 10 Κ3 (ΡΝ) 18.5 PZU-V2-N 10 V0Dt iV) 16.1 CPTP-301 5 AVoot (V) 8.5 CPTP-302 5 (ms) 8 CPTP-303 5 γι (mPa.s) 452 PTP-102 5 PTP -201 5 PTP-301 — 5 PTP-302 5 CCPC-33 5 CCPC-34 5 CCPC-35 5 Total 100 88881.doc 78- 1342330 Example 9 Amount of compound (wt./.) Tni (0〇96.2 ME2N.F 12 Δε 47.0 ME3N.F 12 Δη 0.1508 ME4N.F 12 Κι (pN) 7.9 ME5N.F 12 K3 fpN) 21.8 HP-3N.F 5 V〇〇t (V) 11.6 HP-4N.F 5 AVoot (V) 2.2 HP-5N.F 5 T〇Dt (ms) 47 CCG-VF 15 CCPC-33 2 CCPC-34 2 CCPC-35 2 CCP-V-1 8 CCP-V2-1 A 8 Total 100 Example 1 0 Compound amount (wt%) Tn, (°C) 98.1 ME2N.F 10 Δε 46.3 ME3N.F 10 Δη 0.1439 ME4N.F 10 Κι (pN) 8.5 ME5N.F 10 K3 (PN) 18.4 PZU- V2-N 10 Voot (V) 11.8 CCG-VF 10 △VODt (V) 6.5 CCP-V-1 5 T〇Dt (mS) 49 CCP-V2-1 5 CVCP-V-1 5 CVCP-V-01 5 CVCP-1V-01 5 CCPC-33 5 CCPC-34 5 CCPC-35 5 Total 100 88881.doc -79- 1342330 Example 11;, amount of compound (wt%} Tn, (°C) 99.2 ME2N.F 10 Δε 43.3 ME3N.F 10 Δη 0.1453 ME4N.F 10 Κτ (pN) 9.8 j ME5N.F 10 K3 (PN) 12.7 PZU-V2-N 10 V〇nt (V) 14.9 HP-33 10 T〇Dt (ms) 54 HP -53 10 HD-34 10 HD-35 10 CP-33 5 CP-35 5 Total 100 Example 12 Quantity of compound (wt%) Tni (°C) 99.1 ME2N.F 10 Δε 41.6 ME3N.F 11 Δη 0.1690 ME4N.F 11 Κτ (ρΝ) 7.9 ME5N.F 11 Κ3 (ρΝ) 18.3 HP-3N.F 5 V〇〇t (V) 13.9 HP-4N.F 5 T〇pt (rns) 25 HP-5N.F 5 巳CH -2F.F 9 巳CH-3F.F 9 BCH-5F.F 9 CBC-33F 5 CBC-35F 5 CBC-55F 5 Total 100 8888l.doc -80- 1342330 Example 1 3 _ Compound amount (wt%)Tni (°C) 99.0 PZU-V2-N 14 Δε 39.1 ME2N.F 8 Δη 0.1234 ME3N.F 8 Κι (ρΝ) 9.9 ME4N.F 8 Κ3 (ΡΝ) 13.0 ME5N.F 8 V〇〇t (V) 17.1 HD-34 11 AV0Dt (V) 29.4 HD-35 11 T〇Dt (ms) 27 CC-5-V 17 J CCPC-33 5 CCPC-34 __ 5 CCPC-35 5 Total 100 B8881.doc -81 - 1342330 Examples 14 Compound amount (wt%) TN. (°C) 95.4 P2U-V2-N 15 Δε 40.1 ME2N.F 5 Δη 0.1176 ME3N.F 5 Κτ (ρΝ) 8.0 ME4N.F 5 Κ3 _ 15.9 ME5N.F 5 V〇 〇t (V) 7.7 CCPC-33 4.5 △v00t (V) 36.2 CCPC-34 4.5 τ〇〇( (ms) 36 CCPC-35 4.5 CCP-V-1 4 CCP-V2-1 4 CC-5-V 1〇CBC-33F 2 CBC-35F 2 CBC-55F 2 CDU-2-F 5 CDU-3-F 5 CDU-5-F 5 CCZU-2-F 3 CCZU-3-F 6.5 CCZU-5-F 3 Total 100 82- 88881.doc 1342330 Example 1 5 Quantity of compound (wt. /. 〉 Tn, (°C) 98.1 PZU-V2-N 20 Δε 44.5 ME2N.F 5 Δη 0.1536 ME3N.F 5 Κ! (ρΝ) 8.7 ME4N.F 5 Κ3 (ρΝ) 11.9 ME5N.F 5 V〇nt (V 11.5 BCH-2F.F 10 AV00t (V) 3.5 巳CH-3F.F 10 t〇〇t (rns) 19 BCH-5F.F 10 BCH-32 5 BCH-52 10 CCPC-33 5 CCPC-34 5 CCPC-35 - 5 Total 100 Example 1 6 Compound amount (wt%) Tn, (°C) 101.4 PZU-V2-N 20 Δε 42.9 DU-3-N 10 Δη 0.1011 CCGU-3-F 5 Κ! (ρΝ) 5.8 CCZU-2-F 7 K3 _ 16.9 CCZU-3-F 15 Vont (V) 6.8 CCZU-5-F 7 AV0Dt (V) 53.1 CCQU-2-F 7 T〇〇t (ms) 42 CCQU-3- F 7 CCQU-5-F 7 CCPC-33 5 CCPC-34 5 CCPC-35 5 Total 100 8888l.doc •83- 1342330 Example 17 Quantity of compound (wt%) Tn. (°C) 99.0 PZU-V2-N 15 Δε 44.8 ME2N.F 5 Δη 0.1177 ME3N.F 5 κ, (ρΝ) 6.4 ME4N.F 5 Κ3 (ΡΝ) 16.1 ME5N.F 5 V〇Dt (V) 8.2 CDU-2-F 5 AVnDt (V) 40.2 CDU -3-F 5 τ〇〇ι (ms) 51 CDU-5-F 5 CCGU-3-F 6 CCZU-2-F 7 CCZU-3-F 15 -- CCZU-5-F 7 CCPC-33 5 CCPC -34 5 CCPC-35 5 Total 100 84- 88881.doc 1342330 Example 1 8 Compound amount (Wt0/o) Tn, (°C) 102.0 PZU-V2-N 15 Δε 44.7 ME2N.F 5 Δπ 0.1289 ME3N.F 5 Κι (ρΝ) 7.2 ME4N.F 5 Κ3 (ΡΝ) 16.2 ME5N.F 5 V〇〇t (V) 5.3 CGU-2-F 5 AV〇Dt (V) 40.3 CGU-3-F 5 :〇Dt (ms) 34 CGU-5-F 5 CCGU-3-F 5 CCZU-2 -F 5 CCZU-3-F _ 10 CCZU-5-F 5 CCP-V-1 5 CCP-V2-1 5 CCPC-33 5 CCPC-34 5 CCPC-35 5 Total 100 88881.doc 85- 1342330 Examples 19 amount of material (wt%) Tni (°C) 96.9 PZU-V2-N 15 Δε 49.6 ME2N.F 5 Δη 0.1399 ME3N.F 5 Κι (pN) 7.2 ME4N.F 5 K3 (PN) 15.7 ME5N.F 5 V〇〇t (V) 7.0 PGU-2-F 5 △V0Dt (V) 32.2 PGU-3-F 5 x〇Dt (ms) 31 PGU-5-F 5 CCGU-3-F 5 CCZU-2-F 6 CCZU-3-F 13 CCZU-5-F-6 CCP-V-1 5 CCPC-33 5 CCPC-34 5 CCPC-35 5 Total 100 Example 20 Quantity of compound (wt%} Tni (°C) 96.4 PZU- V2-N 20 Δε 47.6 ME3N.FF 10 Δη 0.1327 CGU-2-F 10 Κι (pN) 7.9 CGU-3-F 10 K3 (pN) 18.0 CGU-5-F 10 V〇〇, (V) 4.1 CCGU- 3-F 5 Δν00( (V) 26.1 CCP-V-1 10 (ms) 36 CCP-V2-1 10 CCPC-33 5 CCPC-34 5 CCPC-35 5 Total 100 88881.doc -86- 1342330 Example 2 1 Compound amount (wt%) Tni (°C) 98.3 PZU-V2-N 21 Δε 43.9 ME2N.F 5 Δη 0.1355 ME3N.F 5 Κτ (pN) 8.5 CGU-2-F 10 K3 (PN) 19.0 CGU-3-F 10 V〇at (V) 4.0 CGU-5-F 10 △V00t (V) 27.7 CCGU-3-F 4 T〇Dt (rnS) 28 CCP-V-1 10 CCP-V2-1 10 CCPC-33 5 CCPC-34 5 CCPC-35 5 Total — 100 Comparative Example MLC-6204 was tested under similar conditions to the examples of the present invention (Merck KGaA, Darmstadt) ):

Tni (°C) 62.4 Δε 35.2 Δη 0.1484 Κι (pN) 7.5 K3 (PN) 14.8 V〇〇t (V) 11.8 AV0Dt (V) 7.3 T〇Dt (ms) 41 γι (mPa.s) 358 88881.doc 87 · j34233〇 [Simplified Schematic] Figure 1 illustrates the pole double stability using grating alignment (line indicates local guide), showing a) high tilt (continuous) and b) low tilt (defect) states. Figure 2 shows the guide distribution of the high and low dip state for a) BD and b) TN geometry for ZBD. Figure 3 shows the MLC-62〇4-〇00 at 25. r r_v curve (pulse persistence or time slot relative voltage). The switching voltage % used for comparison and the operating window (Δν400 “) are displayed. 88881.doc -88 -

Claims (1)

1342330 Patent Application No. 092134836. Chinese Patent Application Substitution (October 1999) ___ Pickup, Patent Application Range: 丨1. Use of a m' composition after a double stable state, the composition comprising: 30 weight. a component (α) of 〇 (based on the total weight of the composition) containing one or more compounds having a dielectric anisotropy Δ ε of at least 25, wherein at least 25 5% by weight (based on the total weight of the composition) a compound having a dielectric anisotropy Δ ε of at least 40; and at least 5% by weight (based on the total weight of the composition) of the component (β); wherein the component (β) comprises at least one compound of the formula III and/or at least A compound of the formula IV and/or at least one compound of the formula v and/or at least one compound of the formula VI and/or at least one compound of the formula VII: Where a and b are independent of each other as 0 or 1; 88881-991021.doc 1342330 IV, K', R71 and r72 are each independently a Cl-ClS alkyl group which is unsubstituted or mono- or poly-substituted by cn or halogen and wherein one or more c H 2 groups can be independently of each other -〇- , _S-, -CH=CH-, -C = C-, -CO-O-, -0C-0- substitution, such that the heteroatoms are not adjacent to each other: Η or F; Z41 4_co-〇-, -ch2〇-, -〇ch2-, -cf2o-, _〇cf2- '-CH2CH2- '-CF2CF2- > -CH2CF2- ' -cf2ch2-, -CH=CH- or -C three C-; 2. The use of the liquid crystal composition of claim 1 wherein the double stable liquid crystal device is a pole double stable nematic liquid crystal device. 3. The use of a liquid crystal composition according to claim 1 or 2, wherein the component (α) comprises at least one compound of the formula I and/or at least one compound of the formula II: 88881-991021.doc 1342330 Z-CN c ' d R" II e and f are independent of each other as 0 ' 1, 2, 3 or 4; for Ci C15, the base is 'unsubstituted or via (3) or south single or multiple-substituted and one or more of them The CH2 groups may be independently replaced by _ 0 S- ' -CH=CH- ^ -C=C- ^ -CO-0- ^ -0C-0-1 such that the heteroatoms are not adjacent to each other; C2C1S alkenyl , which is unsubstituted or mono- or poly-substituted by halogen or wherein - or a plurality of eh groups are independently of each other via _ ° , -CH=CH-, -OC-, -CO-O-, -OC- 0-substitution' is such that the heteroatoms are not adjacent to each other; Zn and Z21 are each independently a single bond or _c=c. 4. The use of the liquid crystal composition of claim 1, wherein the component (α) comprises at least one compound of the formula VIII: Z-CN g and h R81 VIII are each independently 〇, i, 2, 3 or 4; are a Ci alkyl group which is unsubstituted or cn or halogen alone 88881-991021.doc 1342330 or poly-substituted and one of Or a plurality of ch2* may be independently substituted with each other by _ 0-, -S-, -C^c-, -CO-O-, -0C-0- such that the heteroatoms are not adjacent to each other; Z81 is a single bond or - C^c-. The use of the liquid crystal composition of claim 1, wherein the component (α) comprises at least one compound of the formula IX: Wherein j is 0 or 1; R91 is a Ci-Cu alkyl group which is unsubstituted or mono- or poly-substituted by CN or halogen and wherein one or more CH 2 groups are via -Ο-, -S-, - CH=CH-, -C tri C-, -CO-O-, -0C-0- substitution such that the heteroatoms are not adjacent to each other; Z91 and Z92 are each independently a single bond or -ChC-; 88881-991021.doc 1342330 Lyi, L92 'L93 and L94 are independent of each other as H or F. 6. The use of the liquid crystal composition of claim 1, wherein the liquid crystal composition further comprises: at least 3% by weight (based on the total weight of the composition) of the component (γ), which has one or A compound having an optical anisotropy Δη of at least 0.20. 7. The use of the liquid crystal composition of claim 6 苴 (7) includes at least one compound of the formula: ^ R101 and RL are independently of each other (^-(:15 alkyl, 1 CN or halogen mono- or poly-substituted and one of them -Ο-, -S-, -CH=CH-, -CsC_, -S-, - CH=CH-〇-substitution, either unsubstituted or via multiple CH2 groups, -CO-O-, -OC- Replacement ' makes the heteroatoms not adjacent to each other The use of the crystalline composition, wherein the liquid compound of the formula XI and/or at least one liquid crystal composition as in the first aspect of the patent application comprises at least one of 88881-991021.doc 1342330 a compound of the formula XII and/or at least _; VTT λ / hopper, s - a compound of the formula XIII and / or at least one compound of the formula XIV: Wherein R and R14 2 are independently of each other as c CN or halogen single- or more independently from each other by -0, 2_C丨5 alkenyl which is unsubstituted or trans-substituted and wherein one or more CH 2 groups are -S-, _CH=CH-, -C=C-, -CO- 〇- '-OC-0- Substituting 'so that the heteroatoms are not adjacent to each other; R121 ' R131 > r'32 „ Rui „ , and R are each independently a Ci-Cu alkyl group which is unsubstituted or substituted by CN or halogen mono- or poly- The one or more CH2 groups may be independently substituted with each other by -〇-, -s-, _CH=CH., -bC-, -C0_0_, _〇c_〇_ such that the heteroatoms are not adjacent to each other; -C!5 phenotype, which is unsubstituted or mono- or poly-substituted by halogen and one or more of them can be independently of each other _〇..._s_, -CH=CH-, -CEC-, _C0_0_ ' _OC _〇•Replacement, so that 88818-99102l.doc 1342330 heteroatoms are not adjacent to each other; γ11丨 is f, cn, independently mono- or poly-substituted C1-C15 alkanoyl or C2 -C15 alkenyl, or mono- or poly-substituted by halogen (: 丨-(:15 alkoxy; Lm and L112 are each independently η or F; and independently of each other or 9_ as in the scope of claim 1 Use of the liquid crystal composition, wherein the liquid crystal composition comprises at least 50 weight % (based on the total weight of the composition) of the component (4). The use of the liquid crystal composition of claim i, wherein the liquid crystal composition comprises at least 50% by weight of the total weight of the composition. The composition of the component (c〇' at least 30% by weight (based on the total weight of the composition) has a dielectric anisotropy Δ ε of at least 40. 11. The liquid crystal composition of claim 1 Use of the liquid crystal composition comprising at least one compound of the formula II of the component (α) and at least 8% by weight (based on the total weight of the composition) of the component (β). The use of the liquid crystal composition of the invention, wherein the liquid crystal composition comprises at least 5% by weight (based on the total weight of the composition) of the component (γ). 13. The use of the liquid crystal composition of claim 1 Wherein the liquid crystal composition comprises at least one formula XV and/or formula XVI and/or formula XVII and/or formula XVIII and/or formula XIX and/or formula XX and/or formula amp & / or formula 88881-991021.doc 1342330 XXII compound: XVI XVII XVIII XIX XX XXI XXII wherein R..., R丨72, Rm, R丨82, R201, R21 丨 and r221 88881-991021.doc are independent of each other as c! -C! 5 alkyl, which is unsubstituted Or by CN or a single or multiple-substituted and one or more CH2 groups can be independent of each other... -S_, _CH=CH-, -C three C-, -C0-0-Rm '·〇〇〇·substitution, such that the heteroatoms are not adjacent to each other; SCrC!5 alkyl, which is unsubstituted or mono- or poly-substituted by cn or halogen and wherein one or more of CH 2 can be independently of each other - 〇-, -S-, -CSC-, ·(:0-0-,-0C-0- substitution, so that the heteroatoms are not adjacent to each other; f161, Y191, Υ201' γ211 and γ221 are independent of each other, F, ci, Independent of each other by a halogen mono- or poly-substituted Cl_Cl5 alkane or C2-Cls alkenyl, or a halogen mono- or poly-substituted Cl_C15 alkanoyl; Lm, Lm, L192, L201 L202 L203, L204, L211 L212, and L224 L213, L214, L·215, L·216, L·221, L222, L·223 are each independently H or F; Is -CO-O-, CH2◦ or cf2o. 14. A liquid crystal medium comprising: at least 15% by weight of at least one compound of the formula: Wherein c and d are each independently 〇, i, 2, 3 or 4; R11^alkyl, which is unsubstituted or mono- or poly-substituted by cn or halogen and wherein one or more CH2 groups are independently of each other -88881-991021.doc 1342330, -CH=CH-, -CeC-, -CO-O-, -OC-O-substitution" such that the heteroatoms are not adjacent to each other; and Z is a single bond or. and 5 to 30 % by weight of at least _ formula u compound: e and ί are each independently 〇, 1, 2, 3 or 4; R is a C2-Cl5 alkenyl group which is unsubstituted or mono- or poly-substituted by CN or halogen and wherein one or more CH 2 groups are each other Independently _ 〇-, -CH=CH-, -C tri-C-, -CO-O-, -OC-O-substitution" such that the heteroatoms are not adjacent to each other; and Z is a single bond or -CsC stomach; and At least 5% by weight - or a plurality of compounds of formula IIID or formula IIIE: R31 and R32 are independently of each other (: 丨-(:15 alkyl, which is not taken 1 乂 or via 88881-99l02l.doc • 10· 15. CN or halogen early- or poly-substituted independently of each other 〇_ , _S_, and one or more of the CH 2 groups may be -CH=CH- ' -C^C- ' -CO- 0-, -0C-0-, such that the heteroatoms are not adjacent to each other. It comprises: 5 to 30% by weight of at least one compound of the formula π: e and f R21 Z2 and are independent of each other! , 2, 3 or 4; is a C2 Cl5 alkenyl group which is unsubstituted or mono- or poly-substituted by CN or halogen and wherein one or more CH 2 groups are independently of each other. 〇-, -S-, - CH=CH·, CEC, c〇〇〇 are substituted such that the heteroatoms are not adjacent to each other; and are a single bond or —CsC—; at least 20% by weight of at least one compound of the formula VIII: g and h R81 VIII are independently of each other, 1、, 1, 2, 3 or 4; are CI Cl5 alkyl groups which are unsubstituted or mono- or oxi-substituted with CN or halogen and wherein - or more than one CH 2 group may be independent of each other By S 88881-991021.doc • 11 · 1342330 〇-, -s·, -c three c-, <〇·〇_, _oc_〇_ substitution, so that the heteroatoms are not adjacent to each other; and are early bonds or -C Ξ C -; and 11 and Han are independently of each other as a C1-C"alkyl group which is unsubstituted or mono- or poly-substituted by CN or halogen and wherein one or more CH2 groups may be independent of each other - Ο-, -s-, -CH =CH-, -CeC-, -CO-O, -0C-0- substitutions such that the heteroatoms are not adjacent to each other. 16. A dual stable liquid crystal device comprising: two external substrates, which form a liquid crystal cell together with the frame; a liquid crystal composition in the liquid crystal cell; an electrode structure having an alignment layer on the inside of the external substrate, At least one of the alignment layers includes an alignment grating that can cause the liquid crystal composition to adopt at least two different stable states, wherein the assembly of the electrode structure and the alignment layer enables switching between the at least two different stable states The electrode structure is achieved by applying a suitable electrical signal; wherein the liquid crystal composition comprises: at least 30% by weight (based on the total weight of the composition) of the component (4), which has 8881-991021.doc -12- 1342330 containing one or more a compound having a dielectric anisotropy Δ ε of at least 25, wherein at least 25% by weight (based on the total weight of the composition) of the compound has a dielectric anisotropy Δ ε of at least 40; and at least 5% by weight (based on the total of the composition) Component (β); wherein the component (β) comprises at least one compound of the formula III and/or at least one compound of the formula IV and/or at least one compound of the formula V and/or at least one formula VI Compounds thereof and / or at least one compound of formula VII: Where a and b are independent of each other by 0 or 1; R R41 RRRR 61 R 62 R71 and R are each independently a Cl-Cl5 alkyl group which is unsubstituted or mono- or poly-substituted by cn or a lignin and one or more of which may be independently of each other - 〇- , -s-, _CH=CH·, «·, c〇〇_, -OC-O- substitution, such that the heteroatoms are not adjacent to each other; 88881-99l021.doc -13· 1342330 is Η or F; is _( ^0-0-, -(^1^2〇-, -〇€1^2-, -匸卩2〇-, -0[?2-, -CH2CH2-, _cf2cf2-, _ch2cf2-, -cf2ch2- , -CH=CH· or -C^C-; Wherein L32 and L33 are independent of each other as H or F. 17. The dual steady state liquid crystal device of claim 16, wherein the device is a pole double stable nematic liquid crystal device; and the electrode structure having an alignment layer on the inside of the outer substrate has at least one alignment layer Included is an alignment grating that allows at least two different steady state states of the compound of the liquid crystal composition to have different pretilt angles on the same azimuth plane. 1 8. The dual steady state liquid crystal device according to claim 16 or 17, wherein the component (α) comprises at least one compound of the formula I and/or at least a compound of the formula π: 88881-991021.doc -14 - Wherein df is independently 0, 1, 2, 3 or 4; Ri丨 inflammation C! C! 5 alkyl, which is unsubstituted or substituted by cN or halogen, or one or more CH2 groups Independently, 0-, -s-, -CH=CH..."·, _c〇〇, 〇c 〇 may be substituted such that the heteroatoms are not adjacent to each other; R is a C2_Cl5 alkenyl group which is unsubstituted or CN or _mono- or poly-substituted and one or more of the CH2 groups may be independent of each other via j 〇, -S-, -CH=CH...-C three c_, _c〇-〇-, ·〇〇〇 The substitution 'so that the heteroatoms are not adjacent to each other; Z and z21 are each independently a single bond or _Csc-. 19. The dual steady state liquid crystal device of claim 16, wherein the component (α) comprises at least one compound of the formula: g and h are each independently 〇, 1, 2, 3 or 4; VIII RS is a C"Cl5 alkyl group which is unsubstituted or substituted by CN or halogen single 88881-99J021.doc -15- 1342330 or eve- And one or more of the cH2 groups may be independently substituted with each other via _ 〇 _, _s_ ' ... _c 〇〇 _, 〇 c , such that the hetero atoms are not adjacent to each other; Z is a single bond or -CsC-. The dual stable liquid crystal device of claim 16, wherein the component (α) comprises at least one compound of the formula: IX J is 0 or 1; R91 is a Cl_Cl5 alkyl group which is unsubstituted or mono- or poly-substituted by CN or dentate and one or more of Ch can pass _〇·, _s_, _ CH=CH- , AC · m _ 〇 c 〇 replacement so that the heteroatoms are not adjacent to each other; Z91 and Z92 are independent of each other as a single bond or -Cs (%; 8888l-991021.doc -16· 1342330 Wherein L·91, L·92, L93 and L94 are each independently H or F. 21. The dual steady state liquid crystal device of claim 16, wherein the liquid daily composition further comprises: at least 3% by weight (based on the total weight of the composition) of a component ([gamma]) comprising one or more A compound having an optical anisotropy Δη of at least 0.20. 22. A dual steady state liquid crystal device according to claim 21, wherein the component ([gamma]) comprises at least one compound of formula X: Wherein k is 〇, 1, 2, 3 or 4; R and R are each independently a ci_ci5 pit group which is unsubstituted or single- or poly-substituted by CN or a functional group and wherein one or more CH 2 groups are -〇-, -S-, _CH=CH_, _CEC·, c〇〇_ 〇c O-substitution, such that the heteroatoms are not adjacent to each other; and are or 〇23. The double stable state of claim 16 The liquid crystal device further comprising at least one compound selected from the group consisting of a compound of the formula and/or 88881-99102l.doc -17 1342330 at least one compound of the formula XII and/or at least one compound of the formula 及πι and/or at least one formula Compound of XIV: R " and R"2 are each independently a C2-Cl5 thin group which is unsubstituted or substituted by CN or a single or multiple and one or more CH2 groups may be independently of each other by -0-, - S_ ' _CH=CH, c〇〇-, -OC-O- substitution, such that the heteroatoms are not adjacent to each other; R1 d32 and R(4) are independently of each other Ci_Ci5 alkyl, which is unsubstituted or via CN or a single element - Or more than _ substituted and one or more of the CH2 groups may be independently replaced by 〇_, _s_, , "-, -co-o-, _oc_0_ such that the heteroatoms are not adjacent; R122 is ^·^ a 5-alkyl group which is unsubstituted or mono- or polysubstituted by a sulphate and wherein one or more CH 2 groups are independently of each other via _〇_, S-, -CH=CH-, -OC-, -CO- O-, such that the heteroatoms are not adjacent to each other; -0C-0-substitution 8888I-99102I.doc -18- 1342330 is a Ci-Ci5 alkane or C2-CM which is independently mono- or polysubstituted by halogen, F, Cl An alkenyl group, or a mono- or poly-substituted alkoxy group; Independent of each other as Η or F; and Independent of each other 24. The dual steady state liquid crystal device of claim 6, wherein the liquid crystal composition comprises at least 50% by weight (based on the total weight of the composition) of 6 mystery components (α). 25. The dual stable liquid crystal device of claim 16, wherein the liquid crystal composition comprises at least 50% by weight (based on the total weight of the composition) of the component (α), wherein at least 30% by weight The compound of the total weight of the composition has a dielectric anisotropy Δ ε of at least 40. 26. The dual steady state liquid crystal device as claimed in claim 16, wherein the liquid crystal composition comprises at least one compound of the formula II of the component (α) and at least 8% by weight (based on the total weight of the composition) Ingredient (β). 27. The dual steady state liquid crystal device as claimed in claim 21, wherein the liquid crystal composition comprises at least 5 by weight. / ◦ (based on the total weight of the composition) of the composition (γ Ρ 28. The double stable liquid crystal device of claim 16 wherein the liquid crystal composition comprises at least one selected from the group consisting of Formula XV and/or Formula XVI And/or formula xvii and/or formula xviii and/or formula XIX and/or formula XX and/or formula ΧΧΙ and/or compound of formula XXII: 88881-99102I.doc • 19- xv1342330 XVI XVII XVIII XIX XX XXI XXII wherein R151, R161, R171, R172, Rm, R182, R201, R2" and R221 are each independently a CrCb alkyl group which is unsubstituted or via CN·20·88881-991021.doc 丄 or a protein early- or And the one or more of the CH2 groups may be independently substituted with each other by -〇-, _S~CH=CH...try-c〇〇·J9 〇c-o_ such that the heteroatoms are not adjacent to each other; RJ y 1 a ', hC a 5-alkyl group which is unsubstituted or mono- or poly-substituted by cN or halogen and wherein one or more CH 2 * can independently pass each other · 〇 _ , Ί ' _ 〇 C_ ' -CO-O-, ·〇(:_〇_ substitution, such that the heteroatoms are not adjacent to each other (ie, RW is not an alkenyl group); Y15丨, Ym, Ym, γ20, γ2丨丨, and γ22丨 are independent of each other Is F, Cl, independently mono- or poly-substituted Cl_Ci5 alkane or C2_C 5 fluorenyl, or mono- or poly-substituted by halogen (:, 5 alkoxy; L15l, L161, L191, L192, L201, L202, L203, L204, L2H, L212, L213, L214, L215, L2, 6, L2", L222, l223 and L224 are each independently H or F; and Z151 is -CO-O-, ch2o or Cf2o. 88881-991021.doc -21 ·